Hydrochloric Acid → HCID 23372644, compound

HRID 1899104Notes

Reaction equation

HRID 1899104 reaction equation
C([CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][C:14]([C:16]#[N:17])=[CH:13][C:12]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:7][CH:6]=1)=O.Cl>CO.O1CCCC1>[CH3:3][NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:15][C:14]([C:16]#[N:17])=[CH:13][C:12]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23372687HCID 23372687, compound

Product 1

HCID 23372644HCID 23372644, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[4-(N-formylmethylamino)phenyl]-4-[4-(methylsulfonyl)phenyl]thiophene-2-carbonitrile (2.2 g) and concentrated hydrochloric acid (13 ml) in methanol (60 ml) and tetrahydrofuran (40 ml) was stirred at ambient temperature for 2.5 hours. The mixture was concentrated and the residue was triturated in a sodium bicarbonate solution to give a powder. The crude powder was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (4:1) to give a yellow powder of 5-[4-(methylamino)phenyl]-4-[4-(methylsulfonyl)phenyl]thiophene-2-carbonitrile (1.4 g).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was triturated in a sodium bicarbonate solution
  3. customto give a powder
  4. customThe crude powder was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-a70a49d22ade4814b3790263732a79d6
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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